5-(4-Methyl-pentyl)-1a,7a-dihydro-1-oxa-cyclopropa[b]naphthalene-2,7-dione | 500217-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(4-Methyl-pentyl)-1a,7a-dihydro-1-oxa-cyclopropa[b]naphthalene-2,7-dione
• 英文别名: 4-(4-Methylpentyl)-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
• CAS: 500217-63-0
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: SPAWXBNEEABHEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-Methyl-pentyl)-1a,7a-dihydro-1-oxa-cyclopropa[b]naphthalene-2,7-dione 在 硫酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-hydroxy-6-(4-methylpentyl)-1,4-naphthoquinone 、 1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)- 、 2,3-dihydroxy-6-(4-methylpentyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m
• 作为产物：
  描述：

  1,4-Naphthalenedione, 5,8-dihydro-6-(4-methyl-3-pentenyl)- 在 Lindlar's catalyst manganese(IV) oxide 、 氢气 、 双氧水 、 sodium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 97.0h， 生成 5-(4-Methyl-pentyl)-1a,7a-dihydro-1-oxa-cyclopropa[b]naphthalene-2,7-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

文献信息

• Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones
  作者：José M. Miguel del Corral、Maria Angeles Castro、Marina Gordaliza、Maria Luz Martin、Alaide B. Oliveira、Simone A. Gualberto、Maria Dolores García-Grávalos、Arturo San Feliciano

  DOI：10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

  日期：2002.12

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.